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Details

Stereochemistry ACHIRAL
Molecular Formula C15H24O
Molecular Weight 220.3505
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYLATED HYDROXYTOLUENE

SMILES

CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C

InChI

InChIKey=NLZUEZXRPGMBCV-UHFFFAOYSA-N
InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

HIDE SMILES / InChI

Molecular Formula C15H24O
Molecular Weight 220.3505
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Butylated hydroxytoluene, commonly known as BHT, is an organic compound that is used in the food, cosmetic, and pharmaceutical industry as an antioxidant. BHT is a substituted derivative of phenol. BHT helps to prevent the formation of free radicals and oxidation. When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins. It may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms. The ability of oral BHT to lead to cancer is a controversial topic, but most food industries have replaced it with butylated hydroxyanisole (BHA). BHT was first used as an antioxidant food additive in 1954. BHT does have other commercial uses, as in animal feeds and in the manufacture of synthetic rubber and plastics, where it also acts as an antioxidant. The U.S. Food and Drug Administration has deemed that BHT is safe enough when used in limited concentrations. It currently permits its use in concentrations of about 0.01% to 0.02% in most foods. As an emulsion stabilizer in shortening, it may be used in a somewhat higher concentration, 200 parts per million.

CNS Activity

Curator's Comment: It may cross the blood brain barrier, causing psychotropic symptoms

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibition by butylated hydroxytoluene and its oxidative metabolites of DMBA-induced mammary tumorigenesis and of mammary DMBA-DNA adduct formation in vivo in the female rat.
1992 Jun
MAP: microwave-assisted extraction of fatty acids and Py/GC/MS analysis of selected insects.
2001
Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay.
2001 Feb
Heteropteris aphrodisiaca O. Machado : effects of extract BST 0298 on the oxidative stress of young and old rat brains.
2001 Nov
[Determination of 2,6-di-tertbutyl-4-methylphenol in an aviation jet fuel by high performance liquid chromatography].
2002 Jul
Hydrogen bonding between phenols and fatty acid esters: (1)H NMR study and ab initio calculations.
2002 Jul 11
A lipoxygenase inhibitor from Aspergillus niger.
2002 Mar
Analysis of the antioxidant butylated hydroxytoluene (BHT) in water by means of solid phase extraction combined with GC/MS.
2002 May
The uptake of tocopherols by RAW 264.7 macrophages.
2002 Oct 15
Contact allergy to the monomers in p-tert-butylphenol-formaldehyde resin.
2002 Sep
Characterization of specifically oxidized apolipoproteins in mildly oxidized high density lipoprotein.
2003 Feb
Sequestering ability of butylated hydroxytoluene, propyl gallate, resveratrol, and vitamins C and E against ABTS, DPPH, and hydroxyl free radicals in chemical and biological systems.
2003 Feb 12
Control of Clostridium perfringens germination and outgrowth by buffered sodium citrate during chilling of roast beef and injected pork.
2003 Mar
A critical evaluation of the factors determining the effect of intramolecular hydrogen bonding on the O-H bond dissociation enthalpy of catechol and of flavonoid antioxidants.
2004 Feb 20
Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites.
2004 Jul
Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress.
2004 Jun
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
Relative antioxidant capacities of propofol and its main metabolites.
2004 Nov
Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation.
2004 Sep 22
New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents.
2006 Aug 15
Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species.
2006 Jul 1
Synthesis and antioxidant activity of [60]fullerene-BHT conjugates.
2006 Jun 2
Cytokine response to lipoprotein lipid loading in human monocyte-derived macrophages.
2006 Jun 26
Evaluation of the antioxidant capacity of limonin, nomilin, and limonin glucoside.
2006 May 31
Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems.
2006 May 31
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Does immune stimulation or antioxidant therapy reduce MNU-induced placental damage via activation of Jak-STAT and NFkappaB signaling pathways?
2007 May-Jun
Patents

Sample Use Guides

The effect of topical therapy with 15% Butylated hydroxytoluene in mineral oil on the course of recurrent herpes simplex labialis was examined in 30 patients in a double-blind, placebo-controlled pilot study.
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment: The effect of Butylated hydroxytoluene on the oxidation of low density lipoproteins in relation to prostacyclin synthesis was investigated in the prescence of rabbit smooth muscle cells (SMC) and Fe-containing culture medium.
Butylated hydroxytoluene (BHT) inhibited lipoprotein oxidation by IC50 values of 0.8 uM
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:02 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:02 GMT 2023
Record UNII
1P9D0Z171K
Record Status Validated (UNII)
Record Version
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Name Type Language
BUTYLATED HYDROXYTOLUENE
FHFI   HSDB   II   MART.   MI   NF   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
Butylated hydroxytoluene [WHO-DD]
Common Name English
BUTYLATED HYDROXYTOLUENE [USP-RS]
Common Name English
INS NO.321
Code English
BUTYLATED HYDROXYTOLUENE [II]
Common Name English
BUTYLHYDROXYTOLUENE [EP MONOGRAPH]
Common Name English
E-321
Code English
PHENOL, 2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-
Systematic Name English
BUTYLATED HYDROXYTOLUENE [VANDF]
Common Name English
BUTYLATED HYDROXYTOLUENE (E 321)
Common Name English
BUTYLATED HYDROXYTOLUENE [FHFI]
Common Name English
BUTYLHYDROXYTOLUENE
EP  
Systematic Name English
2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYLPHENOL
Systematic Name English
BUTYLATED HYDROXYTOLUENE [IARC]
Common Name English
BUTYLATED HYDROXYTOLUENE [MART.]
Common Name English
BHT [FCC]
Common Name English
2,6-DI-TERT-BUTYL-P-CRESOL
Common Name English
KERABIT
Common Name English
BUTYLATED HYDROXYTOLUENE [NF]
Common Name English
4-METHYL-2,6-DITERTIARY-BUTYL-PHENOL
Common Name English
2,6-DI-TERT-BUTYL-P-CRESOL2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-PHENOL
Systematic Name English
NSC-6347
Code English
BUTYLATED HYDROXYTOLUENE [HSDB]
Common Name English
FEMA NO. 2184
Code English
BHT
FCC   INCI  
INCI  
Official Name English
BUTYLATED HYDROXYTOLUENE [MI]
Common Name English
INS-321
Code English
2,6-DITERTIARY-BUTYL-P-CRESOL
Common Name English
BUTYLATED HYDROXYTOLUENE [WHO-IP]
Common Name English
BHT [INCI]
Common Name English
BUTYLHYDROXYTOLUENUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 22105
Created by admin on Fri Dec 15 15:08:02 GMT 2023 , Edited by admin on Fri Dec 15 15:08:02 GMT 2023
JECFA EVALUATION INS-321
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CODEX ALIMENTARIUS (GSFA) INS-321
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NCI_THESAURUS C275
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CFR 21 CFR 172.115
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Code System Code Type Description
CHEBI
34247
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PRIMARY
MERCK INDEX
m2820
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PRIMARY Merck Index
SMS_ID
100000076384
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PRIMARY
ChEMBL
CHEMBL146
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PRIMARY
NSC
6347
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PRIMARY
MESH
D002084
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PRIMARY
EVMPD
SUB11765MIG
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PRIMARY
RS_ITEM_NUM
1082708
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PRIMARY
NCI_THESAURUS
C322
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PRIMARY
DAILYMED
1P9D0Z171K
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PRIMARY
FDA UNII
1P9D0Z171K
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PRIMARY
CAS
128-37-0
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PRIMARY
ECHA (EC/EINECS)
204-881-4
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PRIMARY
EPA CompTox
DTXSID2020216
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PRIMARY
WIKIPEDIA
BUTYLATED HYDROXYTOLUENE
Created by admin on Fri Dec 15 15:08:03 GMT 2023 , Edited by admin on Fri Dec 15 15:08:03 GMT 2023
PRIMARY
RXCUI
1848
Created by admin on Fri Dec 15 15:08:03 GMT 2023 , Edited by admin on Fri Dec 15 15:08:03 GMT 2023
PRIMARY RxNorm
HSDB
1147
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PRIMARY
PUBCHEM
31404
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BUTYLATED HYDROXYTOLUENE
Created by admin on Fri Dec 15 15:08:03 GMT 2023 , Edited by admin on Fri Dec 15 15:08:03 GMT 2023
PRIMARY Description: Colourless crystals or a white or almost white, crystalline powder; odour, faint and characteristic. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS, acetone R, ether R, and arachis oil R. Category: Antioxidant. Storage: Butylated hydroxytoluene should be kept in a well-closed container, protected from light.
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
MAJOR
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IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
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IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.65.pdf